Hydrochloric Acid → HCID 136342249, compound

HRID 447710Notes

Reaction equation

HRID 447710 reaction equation
[OH:1]/[C:2](/[C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)=[CH:3]\[C:4]([C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:7]=1[NH:13][C:14](=S)[S:15]C)=[O:5].C[O-].[Na+].Cl>CO>[OH:5][C:4]1[C:6]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:12])[CH:11]=2)[NH:13][C:14](=[S:15])[C:3]=1[C:2]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)=[O:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 86653096HCID 86653096, compound

Product 1

HCID 136342249HCID 136342249, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Keto-enol 7 (2.12 g, 5.93 mmol) was added to 100 mL of a 0.5 M solution of sodium methoxide in methanol and the mixture was stirred at 0° C. for 3 hours. A 1.0 M solution of hydrochloric acid (53 mL) was poured onto the reaction and the mixture was concentrated to less than half its volume under reduced pressure. The obtained slurry was stirred for 30 min at room temperature and then filtrated. The precipitate was washed with 20 mL of water and 20 mL of methanol, subsequently. The crude product was precipitated from acetone to give 13 as a yellow solid (1.70 g, 93%). mp: 280° C.;

Workup

  1. concentrationthe mixture was concentrated to less than half its volume under reduced pressure
  2. stirringThe obtained slurry was stirred for 30 min at room temperature
  3. filtrationfiltrated
  4. washThe precipitate was washed with 20 mL of water and 20 mL of methanol
  5. customThe crude product was precipitated from acetone

Sources & evidence

ORD record
ord-c31c2a89e94043c695d31fda12bae24c
Source dataset
uspto-grants-2013_07
Patent number
US08481561B2

Reaction notes

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